Highly Regioselective Organocatalytic SNAr Amination of 2,4-Dichloropyrimidine and Related Heteroaryl Chlorides

A highly efficient and regioselective method for the S_NAr amination of 2,4-dichloropyrimidine with oxazolidin-2-one and related weakly nucleophilic amines, using sodium sulfinate and tetrabutylammonium bromide as catalysts, is disclosed. This strategy facilitates the synthesis of various aminopyrimidines in a regio- and chemoselective manner. This approach was successfully used for the amination of various activated N-heteroaromatic substrates.

The use of catalytic amounts of tetrabutylammonium bromide and sodium sulfinate as a temporary nucleophile allows the highly regioselective amination of 2,4-dichloropyrimidine by weakly nucleophilic amines. This protocol proved to be simple, environmentally friendly, and applicable to a variety of amines and activated N-heteroaromatic substrates.

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